Losing It All to Win

This past week, I attended a monthly evening class for a Jesuit leadership program that I’m a part of this year. Our cohort gathered to hear from a panel of three community leaders: one a self-employed consultant for non-profit organizations, one a medical professional in Catholic healthcare, and the third the former principal at Seattle Prep and current teacher there.

At one point, the leader from Seattle Prep shared a story where he was gathered with a number of angry parents from the school community. He recalled, in a state of regret: “There was a turning point in the evening where I realized that I started caring about winning more than anything else.” He looked back on this moment as a failure, explaining that it had prevented him from understanding and improving the situation and from serving his community. He also drove home feeling rotten.

Following the panel, our cohort broke into pairs to discuss highlights. My partner and I spent our allotted time talking about the concept of winning and how it seems to be at the core of so many issues, whether professional or personal. Looking back, in those moments where we prioritized winning in a discussion or argument above seeing the other side, everyone lost. I’ve seen this play out countless times, whether I’m guilty of the habit or I’m on the receiving end. “Eyes on the prize” is a no-win situation, particularly in personal relationships.

A common Jesuit decision-making process involves picturing your funeral and imagining the words that might be used to describe your time on earth. When I apply the exercise to this theme, I’m reminded just how futile the winning mentality is and how little it really gets us. On our death bed, won’t we regret those times that winning pushed away our loved ones? Those times when our scope became myopic at best and we were forced to retreat back to our caves alone; another so-called win on the board and no one to share it with?

While discussing this idea of losing disguised as winning, my partner and I ended up on the subject of Christ’s Crucifixion. Has there ever been a more extreme example of someone who set aside any notion of “winning”? Beyond that, He was indeed the Son of God. Has there ever been a more extreme example of someone being “right”? And despite his right-ness (more than any of us can say in the face of an argument), he still chose to humble himself. There would be no earthly win necessary to secure everlasting life.

This is the way; the earnest walk towards closeness with one another and with God. Yet, we resist and resist every day — we cannot let go of our deep need to win — and we continue to wonder why we find ourselves on the losing end: further from each other, further from God.